Asymmetric Full Saturation of Vinylarenes with Cooperative Homogeneous and Heterogeneous Rhodium Catalysis

Homogeneous and heterogeneous catalyzed reactions can seldom operate synergistically under the same conditions. Here we communicate the use of a single rhodium precursor that acts in both the homogeneous and heterogeneous phases for the asymmetric full saturation of vinylarenes that, to date, consti...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2021-12, Vol.143 (48), p.20377-20383
Main Authors: Wu, Haibo, Yang, Jianping, Peters, Bram B. C, Massaro, Luca, Zheng, Jia, Andersson, Pher G
Format: Article
Language:English
Subjects:
Aromatic compounds
Hydrocarbons
Hydrogenation
Ligands
Organic Chemistry
organisk kemi
Rhodium
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Summary:Homogeneous and heterogeneous catalyzed reactions can seldom operate synergistically under the same conditions. Here we communicate the use of a single rhodium precursor that acts in both the homogeneous and heterogeneous phases for the asymmetric full saturation of vinylarenes that, to date, constitute an unmet bottleneck in the field. A simple asymmetric hydrogenation of a styrenic olefin, enabled by a ligand accelerated effect, accounted for the facial selectivity in the consecutive arene hydrogenation. Tuning the ratio between the phosphine ligand and the rhodium precursor controlled the formation of homogeneous and heterogeneous catalytic species that operate without interference from each other. The system is flexible in terms of both the chiral ligand and the nature of the external olefin. We anticipate that our findings will promote the development of asymmetric arene hydrogenations.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.1c09975